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dc.contributor.author
Riafrecha, Leonardo Ezequiel
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dc.contributor.author
Bua, Silvia
dc.contributor.author
Supuran, Claudiu T.
dc.contributor.author
Colinas, Pedro Alfonso
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dc.date.available
2020-03-16T20:14:51Z
dc.date.issued
2018-02
dc.identifier.citation
Riafrecha, Leonardo Ezequiel; Bua, Silvia; Supuran, Claudiu T.; Colinas, Pedro Alfonso; Improving the carbonic anhydrase inhibition profile of the sulfamoylphenyl pharmacophore by attachment of carbohydrate moieties; Academic Press Inc Elsevier Science; Bioorganic Chemistry; 76; 2-2018; 61-66
dc.identifier.issn
0045-2068
dc.identifier.uri
http://hdl.handle.net/11336/99690
dc.description.abstract
One of the most successful approaches for designing carbonic anhydrase (CA, EC 4.2.1.1) inhibitors was denominated ‘the sugar approach’. The sugar approach consists in attaching different carbohydrates to CA inhibiting pharmacophores for modulating the physicochemical properties of these pharmacological agents. In line with this approach, in this paper, we present a new class of C-glycosides incorporating the sulfamoylphenyl moiety. These compounds have been prepared by sulfamoylation of C-glycosyl phenols, which have been synthetized by aldol reaction of glycosyl ketones with the appropriate aromatic aldehydes. The inhibition profile of the new glycomimetics was determined against four human (h) CA isozymes, comprising hCAs I and II (cytosolic, ubiquitous isozymes), hCA IV and hCA IX (tumor associated isozyme). Peracetylated and deprotected C-glycosyl sulfamates showed better inhibition selectivity compared to structurally related phenylsulfamates. In this study, deprotected compound 12 was identified as selective inhibitor of hCA IX. These results confirm that attaching carbohydrate moieties to CA sulfamoylphenyl pharmacophore improves its inhibitory activity.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Academic Press Inc Elsevier Science
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
CARBONIC aNHYDRASES
dc.subject
C-GLYCOSYL SULFAMATES
dc.subject
CARBOHYDRATE
dc.subject
PHARMACOPHORE
dc.subject
PHARMACOPHORE
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Improving the carbonic anhydrase inhibition profile of the sulfamoylphenyl pharmacophore by attachment of carbohydrate moieties
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2020-03-12T18:43:48Z
dc.journal.volume
76
dc.journal.pagination
61-66
dc.journal.pais
Países Bajos
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dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Riafrecha, Leonardo Ezequiel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.description.fil
Fil: Bua, Silvia. Università degli Studi di Firenze; Italia
dc.description.fil
Fil: Supuran, Claudiu T.. Università degli Studi di Firenze; Italia
dc.description.fil
Fil: Colinas, Pedro Alfonso. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.journal.title
Bioorganic Chemistry
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0045206817306387
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.bioorg.2017.10.020
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